Former president Bill Clinton hopes that Lil Wayne’s release from prison this week will be the last time the Young Money CEO finds himself behind bars.

Clinton made the comment yesterday while making media rounds in Pittsburgh to support the region’s Democratic candidates. The question was initially posed as joke, but Clinton took the opportunity to address Wayne and some of his past comments on Hip-Hop culture.

“My daughter introduced me to rap and Hip-Hop music after I said some things she thought were not very smart,” the former president said on the KISS’s 96.1 Morning Freak Show. “This guy’s smart, and he’s got ability and a new chance now. What I hope is it’s not just something to brand him as a cool guy, but that it’ll never happen to him again.”

In 1992, Clinton became embroiled in controversy when he accused Hip-Hop activist, author and artist Sister Souljah of being a racist comparable to David Duke. He made this accusation after Sister Souljah’s comments criticizing white people and the L.A. Riots. This situation had a lasting impression of U.S. politics, and having a “Sister Souljah moment” became known as any time a political figure renounces a controversial group or person that has associations with their party.

18 years later, Clinton can respect the manner in which Hip-Hop artists tackle social issues. However, he feels that some of them become trapped into a cycle of criminality based on their upbringings.

“I think a lot of these people, like any area of life, don’t get successful by being dumb,” Clinton explained. “They’re really smart, but a lot of them had tough lives and almost think it’s cool to get in trouble every now and then, or they don’t know how to stay out. What I hope will happen is that he has a good life now.”

Lil Wayne’s prison release date may come as early as tomorrow (November 3). His eighth studio album, I Am Not a Human Being, is currently number five on Billbaord’s Top 200.

It’s funny how people hit Clinton with that first “black president” tag during his tenure. Times were different then. Gangsta Rap was seen as the downfall of humanity. For the younger readers, that parental advisory sticker you see on albums now was birthed out of this time period, when you had people like C. Delores Tucker and Tipper Gore actually crusading against record labels and artists who made street music. Clinton kept his distance from Hip-Hop outside of having LL Cool J perform at his 1993 inauguration.